


Condemned to be Free

by VengeanceAngel



Series: Poor Dean [1]
Category: Supernatural
Genre: I was tired when I wrote this so if I need to change a tag, I will if I am told about it nicely, John Winchester's A+ Parenting, M/M, When Wincest appears depends on how hard you're squinting, Will be Wincest eventually, pre-wincest if you squint, season 1 setting
Language: English
Status: In-Progress
Published: 2017-01-02
Updated: 2017-01-02
Packaged: 2018-09-14 08:38:48
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 1,537
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9171172
Author URL: https://archiveofourown.org/users/VengeanceAngel/pseuds/VengeanceAngel
Summary: Dean needs to get free, but what happens when he finally gets his wish?





	

**Author's Note:**

> Heed the warnings, please. Triggers for rape begin with the first sentence. 
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> Disclaimer: I don't own them and never will. No money is being made from this.

Dean cried out again as the man thrust into him harshly. He cursed himself for leaving Sam to sleep while he checked out the local bars for some pool players who could hand some money over to him. Everything had been fine until he wanted to stop playing too suddenly for them. Usually he lost for a bit, then won for awhile, and then started losing again. This way he could play things off like he was quitting before he lost too much back to the guys and that usually appeased the people he played. 

This time he tried to leave right after he'd won quite a bit. He couldn't help it. The guy that he was playing kept brushing up against him and finally Dean had felt the man's erection. He wasn't about to start something so he chose to go. 

The guy acted as if he was fine with Dean leaving and then followed him outside. Before Dean could reach his car he was thrown to the ground by the man who was easily twice Dean's size. He was about to yell out when someone came around the other side of the car and ripped the keys from Dean's clenched fist. He opened the door and helped the first man throw Dean into the car. Dean's head hit the window and it dazed him long enough for both men to get situated in the car. The second man held Dean on his lap in the passenger seat while the first one drove off. 

Dean fumed at this insult. He didn't let anyone drive his Baby except his brother and he was not going to allow this mugging, kidnapping, murder... whatever to happen if he could help it. He began to struggle harder and eventually the guy in the passenger seat who was getting thoroughly beat down, or as much as he could while trying to manhandle a wild and pissed off Winchester, finally yelled at the driver to stop. Dean felt victorious for all of two seconds until he saw that they'd pulled over in an abandoned parking lot of an old factory building that hadn't been used in years. 

"Mark, is he too much for you?" The driver laughed and got out of the car. 

"Yeah, Sam, he's way too much for me." He laughed, too, and Dean struggled harder. 

_Not Sam...any name but Sam._

He broke free and started to run when Sam grabbed him. "Not so fast, boy. We need to have some fun. I'll even let you keep our money if I like having you under me. See how nice I am?"

Dean continued to fight, pulling away from the men and crying out in anger as his shirt was ripped down the middle. It wasn't until the man named Mark started playing with Dean's nipple that he began to come to terms with the fact that this was going to happen. He was stupid for drinking. He was stupid for allowing himself to get too arrogant and getting wasted enough that his ability to free himself was clumsy and weak. He switched from fighting to begging. He refused to cry, but pleaded with the men to let him go, offering up all of the money he had. 

Sam grinned and helped Mark get a hold on Dean before facing him. His tongue snaked out and licked Dean's lips, drawing a shudder from the younger man. "Such a pretty little mouth...." 

He shoved his tongue into Dean's mouth and jammed his thumb and finger into his cheeks to prevent him from biting down. 

Dean gagged as he tasted cigarettes and stale beer on the other man. He was finally forced away from Sam and down to his knees. Sam growled. "Fuck this. I'm not waiting."

Mark smiled. "Hell yeah...it's rare to find one that good."

He held onto Dean's wrists and wrapped an arm around his head as Sam ripped Dean's pants down, having no care for the button that flew off. He tried and tried to shove himself deep into Dean, but he couldn't without hurting himself as well due to the dryness. He fished around in his pockets and pulled out a condom while Mark started beating Dean to keep him down. "Comes with lube..." He chuckled and pulled it on. Mark ceased his attack on the younger man and Sam quickly shoved himself into Dean and listened to the boy howl with the pain. 

Dean closed his eyes and clenched his jaw. He felt himself being ripped apart and felt that he would probably die that night. It wouldn't be a demon or a curse that took Dean Winchester out of this world, but a couple of horny rapists. Dean bit back the cries as the man continued to thrust into him. He had prayed to be free before this had happened, but was now certain that death might be kinder as his spirit shattered.

"Say my name..." 

Dean's eyes snapped open and he shook his head. "No....please..."

Sam immediately began to thrust harder. "Say it and I'll end this for you."

Dean continued to shake his head until he felt a thrust tear him more. Then he allowed himself to sob. "Sam!"

The thrusting eased up and the man smiled. "Sammy...."

Dean choked on his tears and nodded. "Sammy...." Using his baby brother's name with this monster's cock inside of him was too much and he literally felt something snap in his mind. An intent to die had replaced the fear from earlier. Dean knew in that moment that his spirit was already dead. He just needed his body to follow now. There was no way he could ever face his father and brother with this shame.

The rape continued until Sam was satisfied and then he moved to allow Mark a turn. Mark grabbed his own condom and Sam smirked. "Still dry?"

"No, the blood has him lubed up, but...it's blood...I don't know where he's been...You either, for that matter." He slipped on the condom and began to fuck Dean not caring that the boy was now a complete sobbing mess. 

Sam wasn't holding him tight, but he was cradling him as he was being raped again. "Pretty boy...pretty mouth...pretty ass...say my name again."

Dean just started chanting 'Sammy' letting the man think he was obeying when in fact he was calling for help, not aware that Sam Winchester's sixth sense had kicked into high gear the first time he yelled his name. If Dean thought back, it was possible that Dean was not crying for help at all... but redemption. 

Mark was smaller than Sam and began to hit Dean's prostate. Despite the situation, Dean became physically aroused and wanted to die right there and then. But then they all heard the sound of a twig snapping in the distance. Dean was hopeful that it was more men to join in and possibly slit his throat so he could die once and for all.

Mark pulled a gun out of his jacket pocket and held it to Dean's head while Sam knelt down next to Dean who had been pulled upright as a shield for Mark. Sam laughed when he saw the state Dean was in. "Damn...he's hard..." 

He licked Dean's earlobe, convinced that the sound from earlier was a wild animal. "Say my name..."

Dean continued to chant 'Sammy' and begged for mental release, no longer knowing what was happening around him and only feeling the mix of pain and physical pleasure. 

There was a gasp as Mark came hard and then two loud pops. Dean felt Mark slide out of him and he fell to his side, curling up into a ball, still chanting, 'Sammy' and 'Free me.'

Sam Winchester stared at the two bodies, amazed that he had managed to hit Mark in the head when he was so close to Dean. He just hadn't been able to hear the broken cries of his brother calling his name anymore. He wasn't sure what Dean was mumbling about freedom, but he wanted his brother to know he was safe.

He knelt down next to Dean and stroked his hair. "Dean? You're free now..."

Dean continued saying his brother's name and thinking that now he'd much rather be dead as realization hit him. He'd never be free. Sam's rescue had only condemned him with his freedom and he would never be able to say his brother's name again without this moment echoing in his mind. 

Sam pulled Dean's pants up, careful not to jostle him. Dean's chant of "Free me" morphed into "Kill me." Sam wasn't sure how to handle his brother's trauma while he was dealing with his own of seeing his brother being raped and then murdering his violators. Sam kicked the bodies farther away and laid down next to Dean. "Dean...please..." He laid his forehead next to his brother's and just stayed with him, wishing he could summon up the courage to put the gun to Dean's head and pull the trigger, but he couldn't. Instead, he decided that if Dean was condemned to be free, they'd be condemned together.

**Author's Note:**

> I will update this regularly as I first wrote it years ago and am only transferring fics from the original location after I edit them. I apologize if this is choppy, but it's one I enjoyed writing so I wanted it over here on this site.


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